The present invention relates to novel methods and compositions utilizing certain thioesters, a number of which are novel themselves, to alter the flavor and/or aroma of consumable materials.
There has been considerable work on substances which can be used to impart flavors to various consumable materials. These substances are used to diminish dependence on natural materials, some of which may be in short supply, and to provide more uniform properties in the finished product. Vegetable flavors, and particularly alliaceous vegetable flavors, are particularly desirable for many uses in consumable articles.
Furfuryl thioesters have been suggested in United Kingdom Pat. No. 1,156,480 for possible use in coffee flavors. Ethyl-.alpha.-methyldithiopropionate and ethyl-.alpha.-methyldithioisobutyrate have been said to possess green or onion-like fragrance notes, and methanethiol benzoate, methanethiol isovalerate, methanethiol anteisovalerate, methanethiol butyrate, and methanethiol valerate have been said to have milky, rotten egg, cheese or gaseous, cabbage odor-flavor contributions in Netherlands Patent Application No. 68/12,899.
McFadden, et al., Analytical Chemistry 37,560, have suggested the presence of methyl thiohexanoate and thioheptanoate in oil derived from hops, and Buttery, et al., have reported similar work in J. Chromatography 18,399. See also Schultz, Day, and Libbey, The Chemistry and Physiology of Flavors, Westport, Conn.: Avi. 1967, especially at page 412. S-Alkyl derivatives of thioacetic, thioacrylic, and thiobutyric acids have been prepared and are described as disagreeable-smelling liquids. Boehme, et al., Annalen, 648, 15 describes vinyl thioacetate as ill-smelling.
Showell, et al., J. Org. Chem., 27, 2853-8 (1962) show syntheses of cyclohexyl and cyclopentyl thioacetates but do not indicate flavor utility or properties.
Schleppnik and Zenty, J. Org. Chem. 29, 1910-15 (1964) demonstrate syntheses of alkyl(3-alkylthio)thiopropionates via 3-alkylthioacyl chloride intermediates. Synthesis of methyl(3-methylthio)thiopropionate is set out in U.S. Pat. No. 2,888,480. Thioesters are shown in U.S. Pat. Nos. 2,550,141; 2,259,869; and 3,369,979. U.S. Pat. No. 3,103,464 shows various thioesters, including allyl thioacetate, butenyl thioacetate, cyclohexyl thioacetate, and butyl thiobenzoate.